25CN-NBOH hydrochloride
Based on 1 Customer Validation
25CN-NBOH hydrochloride exhibits agonist activity at the 5-HT2a receptor, shows 90- to 100-fold selectivity over the 5-HT2c receptor, and possesses blood-brain barrier permeability. 25CN-NBOH hydrochloride acts as an interoceptive agent with partial agonist-like properties. 25CN-NBOH hydrochloride serves as a pharmacological tool for 5-HT2A receptor research, and its tritiated form functions as a selective agonist radioligand. 25CN-NBOH hydrochloride can be used to investigate diseases characterized by cognitive rigidity, schizophrenia, obsessive-compulsive disorder, depression, pain, inflammation, migraine, and cluster headache.
For research use only. We do not sell to patients.
- Purity : 99.5%
- CAS No.: 1539266-32-4
- Formula: C18H21ClN2O3
- Molecular Weight:348.82
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Storage:Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Biological Activity
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Chemical Information
- Protocols
- Purity & Documentation
- References
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Help & FAQs
All 5-HT Receptor Isoforms
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Biological Activity
Description
IC50 & Target
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Human 5-HT2A Receptor 2.1 nM (EC50) |
Human 5-HT2C Receptor 132 nM (EC50) |
Human 5-HT2A Receptor 8.62 (pEC50) |
Human 5-HT2C Receptor 6.45 (pEC50) |
In Vitro
25CN-NBOH hydrochloride (2 h) is a high-affinity ligand for human 5-HT2AR (Ki = 1.7 nM). In a [3H]Cimbi-36 competitive binding assay using membranes from tsA201 cells transfected with human receptors, 25CN-NBOH shows 76-fold selectivity for human 5-HT2AR over human 5-HT2CR[1].
25CN-NBOH hydrochloride (1 h) is a potent partial agonist of human 5-HT2AR (EC50 = 2.4 nM, achieving 77% of the maximal response induced by 5-HT), while acting as a full agonist of human 5-HT2CR (EC50 = 46 nM, achieving 119% of the maximal response induced by 5-HT), as determined by an IP-One HTRF assay using stable HEK293 cell lines[1].
25CN-NBOH hydrochloride (30 min) is a potent partial agonist of human 5-HT2AR (EC50 = 0.41 nM, achieving 80% of the maximal effect of 5-HT). It also acts as a partial agonist of human 5-HT2CR (EC50 = 5.8 nM, achieving 56% of the maximal effect of 5-HT) in a Ca2+/Fluo-4 assay using stable HEK293 cell lines[1].
25CN-NBOH hydrochloride exhibits high in vitro binding selectivity for 5-HT2AR, with 52-100-fold higher affinity for 5-HT2AR than for 5-HT2CR, 37-fold higher affinity than for 5-HT2BR, and acts as a potent agonist of 5-HT2AR[2].
25CN-NBOH hydrochloride shows 100-fold binding selectivity for human 5-HT2AR over rat 5-HT2CR, with a Ki value of 1.3 nM for human 5-HT2AR and 132 nM for rat 5-HT2CR[3].
25CN-NBOH hydrochloride (30 min) is a potent agonist with 90-fold functional selectivity for human 5-HT2AR over human 5-HT2CR. The EC50 values are 2.1 nM for human 5-HT2AR and 190 nM for human 5-HT2CR[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
In Vivo
25CN-NBOH (0.3-10 mg/kg; i.p.) hydrochloride reduces activity in female NMRI mice in an anxiety-related marble burying assay at doses of 0.3, 1, 3, and 10 mg/kg (i.p.)[1].
25CN-NBOH (0.3-30 mg/kg; i.p.; single dose) hydrochloride induces 5-HT2A receptor-mediated head twitch behavior in Mus musculus, with a maximal response of ~10 head twitches at 1.0 mg/kg, and dose-dependently attenuates DOI-elicited head twitches at doses ≥3.0 mg/kg[2].
25CN-NBOH (0.1-30 mg/kg; i.p.; cumulative dose) hydrochloride produces partial 5-HT2A receptor-mediated generalization to the DOI discriminative cue in mice, reaching a maximum of 55% DOI-appropriate responding at cumulative doses of 10.0 and 30.0 mg/kg[2].
25CN-NBOH (0.1-30 mg/kg; i.p.; cumulative dose) hydrochloride does not generalize to the M100907 discriminative cue in mice, demonstrating no antagonist-like interoceptive effects at 5-HT2A receptors[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6J (male, 6-8 weeks old)[1]
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Dosage:0.51 mg/kg
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Administration:i.p.
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Result:Induced head-twitch response with an ED50 of 1.45 μM/kg.
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Animal Model:NMRI (female, 7-13 weeks old)[1]
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Dosage:0.3 mg/kg; 1 mg/kg; 3 mg/kg; 10 mg/kg
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Administration:i.p.
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Result:Mediated robust reductions in mouse activity in the anxiety-related marble burying assay at doses of 0.3, 1, 3, and 10 mg/kg.
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Animal Model:NIH Swiss (male, 20-25g on delivery)[2]
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Dosage:0.3 mg/kg; 1.0 mg/kg; 3.0 mg/kg; 10.0 mg/kg; 30.0 mg/kg
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Administration:i.p.; single dose
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Result:Elicited significantly more head twitches than saline at 1.0 and 3.0 mg/kg, with a maximum response of ~10 head twitches at 1.0 mg/kg.
Significantly attenuated head twitches elicited by 1.0 mg/kg 25CN-NBOH after pretreatment with M100907.
Did not alter head twitches elicited by 30.0 mg/kg 25CN-NBOH after pretreatment with RS102221.
Dose-dependently suppressed DOI-elicited head twitches at 3.0, 10.0, and 30.0 mg/kg, with 30.0 mg/kg reducing responses to levels significantly lower than all lower doses.
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Animal Model:NIH Swiss (male, food-restricted to 30g during testing)[2]
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Dosage:0.1 mg/kg; 0.3 mg/kg; 1.0 mg/kg; 3.0 mg/kg; 10.0 mg/kg; 30.0 mg/kg
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Administration:i.p.; cumulative dose
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Result:Produced partial generalization to the DOI training cue, eliciting a maximum of 55% DOI-appropriate responding at 10.0 and 30.0 mg/kg, which was significantly more than saline but significantly less than the DOI training dose.
Shifted the dose-effect curve for DOI-like interoceptive effects rightward after pretreatment with M100907, with no statistical significance reached at any dose.
Suppressed response rates at the highest cumulative dose, with 3/6 mice failing to complete the fixed-ratio 5 requirement.\nDid not generalize to the M100907 training cue, eliciting only saline-like responding across all cumulative doses tested.
Produced significantly less M100907-appropriate responding than the M100907 training dose at all doses.
Suppressed response rates at the highest cumulative dose.
Chemical Information
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CAS No. 1539266-32-4
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Appearance Powder
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Molecular Weight 348.82
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Formula C18H21ClN2O3
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SMILES
N#CC1=C(OC)C=C(CCNCC2=C(O)C=CC=C2)C(OC)=C1.Cl
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years In solvent -80°C 6 months -20°C 1 month
Protocols
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Transepithelial/transendothelial electrical resistance assay
TEER measures electrical resistance across epithelial or endothelial monolayers cultured on permeable supports, and the readout reflects ionic conductance through the cell barrier, especially the paracellular pathway regulated by junctional integrity. TEER can be measured without destroying the monolayer and is commonly used before or during transport, permeability, barrier-disruption, and barrier-maturation experiments. TEER values are influenced by biological maturation and technical conditions; reported factors include temperature, medium formulation, passage number, electrode geometry, membrane properties, and junctional length during early monolayer maturation. Therefore, TEER should be interpreted with blank-insert subtraction, area normalization, repeated readings, and, when possible, orthogonal barrier readouts such as FITC-dextran flux or tight-junction staining.
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Research Protocol for Inflammation-related Diseases
The NLRP3 inflammasome is a cytosolic innate immune signaling platform that integrates priming signals and danger-signal activation to promote caspase-1 activation, maturation of IL-1β and IL-18, and gasdermin D-mediated pyroptotic cell death. The core experimental logic is to determine whether inflammatory disease phenotypes are driven by increased NLRP3 expression, ASC-containing inflammasome assembly, caspase-1 cleavage, GSDMD cleavage, and extracellular release of IL-1β/IL-18 rather than by nonspecific cell injury alone. The pathway is strongly linked to inflammation-related disease phenotypes because monosodium urate crystals activate NALP3/NLRP3 inflammasome signaling in gout-like crystal inflammation, cholesterol crystals activate NLRP3 inflammasomes in atherogenesis models, and DSS-induced intestinal inflammation has been reported to involve NLRP3 inflammasome activity. However, experimental colitis studies also show context-dependent protective effects of NLRP3 inflammasome co
Purity & Documentation
References
[2]. Fantegrossi WE, et al. Hallucinogen-like effects of 2-([2-(4-cyano-2,5-dimethoxyphenyl) ethylamino]methyl)phenol (25CN-NBOH), a novel N-benzylphenethylamine with 100-fold selectivity for 5-HT₂A receptors, in mice. Psychopharmacology (Berl). 2015 Mar;232(6):1039-47. [Content Brief]
[3]. Hansen M, et al. Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chem Neurosci. 2014 Mar 19;5(3):243-9. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
25CN-NBOH hydrochloride Related Classifications
HY-103127 Related Classifications
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